Aluminium lithium hydride → 1-Pentanol, 2-amino-3-ethyl-5,5,5-trifluoro-, (2S,3S)-

HRID 1985948Notes

Reaction equation

HRID 1985948 reaction equation
[N:1]([C@@H:4]([C@@H:8]([CH2:14][CH3:15])[CH2:9][C:10]([F:13])([F:12])[F:11])[C:5](O)=[O:6])=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C@@H:4]([C@@H:8]([CH2:14][CH3:15])[CH2:9][C:10]([F:11])([F:12])[F:13])[CH2:5][OH:6]

Participants

4

Conditions

Temperature
40 °C

Procedure

(2S,3S)-2-Azido-3-ethyl-5,5,5-trifluoro-pentanoic acid was dissolved in THF (5 mL) at 0° C. and lithium aluminum hydride (1 M solution in THF) (1 mL, 1 mmol) was added. The resulting solution was stirred at 40° C. for 2 h. The reaction was quenched by sequential addition of water (60 μL), 15% aqueous sodium hydroxide (60 μL), and water (150 μL) with vigorous stirring between each addition. The mixture was then filtered and concentrated to give (2S,3S)-2-amino-3-ethyl-5,5,5-trifluoro-pentan-1-ol.

Workup

  1. customThe reaction was quenched by sequential addition of water (60 μL), 15% aqueous sodium hydroxide (60 μL), and water (150 μL)
  2. stirringwith vigorous stirring between each addition
  3. filtrationThe mixture was then filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-75748648b2d44f988b8832c895872ed2
Source dataset
uspto-grants-2009_06
Patent number
US07547725B2

Reaction notes

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